Synthetic modifications of bifunctional homoallylamines: Synthesis of 2-arylpiperidines, (R)-anatabine and (R)-anabasine |
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Authors: | Jothi L Nallasivam |
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Institution: | Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, MH, India |
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Abstract: | The chiral homoallylamines with orthogonal bifunctional handle, an amine, and a pendant allyl unit are available to be easily converted into N-heterocycles. The N-allylation and Ru-catalyzed ring-closing metathesis delivered the bioactive 2-arylpiperidines, Nicotiana tabacum alkaloids (R)-anatabine and (R)-anabasine in three steps. A formal synthesis of (R)-N-methylanatabine and (R)-N-methylanabasine is also completed. |
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Keywords: | Alkaloids anabasine anatabine homoallylamines metathesis N-heterocycles |
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